Nationally, only half of Latino males graduate from high school (Contreras, 2011). Scholars are beginning to critically examine the various internal and external influences which contribute to low academic achievement for Latino males. This qualitative study uses a human ecological theory to examine how Latino male high school students with high academic achievement understand and develop goals to attend postsecondary education versus engaging in gangs or the military. The findings highlight the students' different levels of college preparation, interactions with military recruitment, and their gang connections.